A highly stereospecific synthesis of (R)- and (S)-[2-2H1]glycine

Armarego, W. L. F.; Milloy, Beverly A.; Pendergast, William

doi:10.1039/p19760002229

Cited by 45 publications

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“…The enantiotopic hydrogens HA and HB in some alcohols (7) and amines (8) have been differentiated by converting them to esters [25] or amides [17] of (-)(1 S,4R)-w-camphanic acid (9). These now diastereotopic hydrogens HA and HB can have quite different chemical shifts when the 'H-NMR spectrum is run in the presence of a lanthanide shift reagent.…”

Section: Resultsmentioning

confidence: 99%

“…The 2-pro-R-specific [26] L-alanine aminotransferase (glutamic-pyruvic transaminase) was used to prepare (2R)- sounded by Armarego et al [17] on the stereochemical purity of [2-'H l]glycines prepared by enzymatic methods, we converted these compounds to their N-camphanoyl amides (12). The 'H-NMR spectra and, more importantly, the 'H-NMR spectra (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…The extracts were dried (Na2S04) and the solvent was removed in vacuo to yield an oil which crystallised on scratching with water,mp67-7O0C(lit. [17]mp73.5-75"C),m/z255(Mt), 6 (C2HC13) for H-2 of glycine 4.14ppm (2H, ABX, N-Camphanoyl-(2 S)-(2-'Hl]glycine (12, HR= 'H).This was prepared from (2R)-[2-ZH,]glycine (11, HR = 'H) using the method described above for the unlabelled compound. Spectra were similar to those of the unlabelled compound but the mass spectral parent ion was one mass number higher, mjz 256.…”

Section: Synthesis Of Labelled 2-aminoethanols (1r)-2-arnino[l-'h]etmentioning

confidence: 99%

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Stereochemistry of the rearrangement of 2‐aminoethanol by ethanolamine ammonia‐lyase

Gani

Wallis

Young

1983

European Journal of Biochemistry

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(1R)‐2‐Amino[1‐2H1]ethanol and (1S,2RS)‐2‐amino[1,2‐2H2]ethanols have been synthesised by decarboxylation of (2S,3R)‐[3‐2H1]serine and (2S,3S)‐[2,3‐2H2]serine respectively. The stereochemical integrity of these labelled 2‐aminoethanols has been ascertained from the 1H‐NMR spectra of their N,O‐dicamphanoyl derivatives. This assay has also been used to confirm that samples of (2R)‐ and (2S)‐2‐amino[2‐2H1]ethanols prepared from (2R)‐ and (2S)‐[2‐2H1]glycines are stereochemically pure. Ethanolamine ammonia‐lyase rearranges (1R)‐2‐amino[1‐2H1]ethanol to acetaldehyde at approximately the same rate as it rearranges unlabelled 2‐aminoethanol, whilst (1S,2RS)‐2‐amino[1,2‐2H2]ethanol is rearranged at the same rate as the (1,1‐2H2)‐labelled substrate. The isotope effect is approximately kH/k2H= 8. The 2H‐NMR spectra of the 3,5‐dinitrobenzoates of the ethanol produced by reduction in situ of the acetaldehyde formed in the rearrangements show that the 1‐2H1 label migrates in (1S,2RS)‐2‐amino‐[1,2‐2H2]ethanol and 2‐amino[1,1‐2H2]ethanol but not in (1R)‐2‐amino[1‐2H1]ethanol. The above results indicate that the adenosylcobalamin‐dependent ethanolamine ammonia‐lyase catalyses the rearrangement of 2‐aminoethanol with migration of the 1‐pro‐S‐hydrogen atom.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Synthesis Of Labelled 2-aminoethanols (1r)-2-arnino[l-'h]etmentioning

confidence: 99%

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Stereochemistry of the rearrangement of 2‐aminoethanol by ethanolamine ammonia‐lyase

Gani

Wallis

Young

1983

European Journal of Biochemistry

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“…Deprotection of a mixture of the cycloadduct 7a has easily been achieved in 94% yield by using a two-step procedure: hydrazinolysis [20] and subsequent saponification on an acidic ion exchange resin. A major disadvantage of this sequence which we up to now have not been able to circumvent is partial epimerization at the stereogenic center C-5 presumably occuring during hydrazinolysis.…”

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confidence: 99%

Synthesis of α‐amino‐3‐chloro‐4,5‐dihydro‐5‐methyl‐5‐isoxazoleacetic acid, a ring‐methylated analogue of the antitumor agent acivicin (AT‐125)

Griesbeck¹,

Hirt²,

Peters³

et al. 1995

Liebigs Ann./Recl.

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a-Amino-3-chloro-4,5-dihydro-5-methyl-5-isoxazoleacetic involving the photoisomerization of N-phthaloylvaline acid (8), a ring-methylated analogue of the potent antitumor methyl ester (1). The stereochemical course of the 1,3-dipolar agent acivicin (AT-125), is synthesized in a 6-step procedure cycloaddition is proven by means of a X-ray structure analyin 63% overall yield from (S)-valine. Key step is the 1,3-dipo-sis of the major diastereoisomer ?a formed in the chloronitrile lar addition of bromonitrile oxide to the N,C-protected (S)-oxide cycloaddition. The absolute configuration of the major isodehydrovaline (6) available from (S)-valine in four steps ( u ) diastereomer ?a and the bromo derivative 7b is (aS,5R).

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“…Thus it can be seen that the retained deuterium atom is in the proR position on this particular methylene group. To determine which deuterium atom of the CH3CD2C02Na is lost and which retained, (2R)-and (2s)-CH3CHDC02Na were made by treatment of (2s)-and (2R)-2-bromopropionic acids with lithium triethylborodeuteride (9). The enantiomeric purities of the resulting monodeuteriated propionate salts were estimated at 96% R and 93% S, respectively, on the basis of the 'H NMR spectra of their esters with methyl (S)-mandelate (10).…”

Section: D2s04mentioning

confidence: 99%

Biosynthesis of the indolizidine alkaloid cyclizidine: incorporation of singly and doubly labelled precursors

Leeper¹,

Shaw²,

Satish³

1994

Can. J. Chem.

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Incorporation of CH313C18O2Na and CD3CH213CO2Na into the indolizidine alkaloid cyclizidine 1, produced by Streptomyces species NCIB 11649, shows that the oxygen attached to C-2 is derived intact from acetate and that the cyclopropyl ring is derived from a single intact propionate unit. However, the level and stereochemistry of the incorporation of deuteriated sodium propionate indicates that it undergoes unexpected modification during incorporation into the cyclopropyl ring.

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A highly stereospecific synthesis of (R)- and (S)-[2-2H1]glycine

Cited by 45 publications

References 0 publications

Stereochemistry of the rearrangement of 2‐aminoethanol by ethanolamine ammonia‐lyase

Stereochemistry of the rearrangement of 2‐aminoethanol by ethanolamine ammonia‐lyase

Synthesis of α‐amino‐3‐chloro‐4,5‐dihydro‐5‐methyl‐5‐isoxazoleacetic acid, a ring‐methylated analogue of the antitumor agent acivicin (AT‐125)

Biosynthesis of the indolizidine alkaloid cyclizidine: incorporation of singly and doubly labelled precursors

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